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Ligands based on polycarb­oxy­lic acids are excellent building blocks for the construction of coordination polymers; they may bind to a variety of metal ions and form clusters, as well as extended chain or network structures. Among these building blocks, bi­phenyl­tetra­carb­oxy­lic acids (H4bpta) with C2 symmetry have recently attracted attention because of their variable bridging and multidentate chelating modes. The new luminescent three-dimensional coordination polymer poly[(μ5-1,1′-biphenyl-2,2′,4,4′-tetra­carboxyl­ato)bis­[μ2-1,4-bis­(1H-imidazol-1-yl)benzene]­dizinc(II)], [Zn2(C16H6O8)(C12H10N4)]n, was synthesized solvothermally and characterized by single-crystal X-ray diffraction, elemental analysis and IR spectroscopy. The crystal structure contains two crystallographically independent ZnII cations. Both metal cations are located on twofold axes and display distorted tetra­hedral coordination geometries. Neighbouring ZnII centres are bridged by carboxyl­ate groups in the synanti mode to form one-dimensional chains. Adjacent chains are linked through 1,1′-biphenyl-2,2′,4,4′-tetra­carboxyl­ate and 1,4-bis­(1H-imidazol-1-yl)benzene ligands to form a three-dimensional network. In the solid state, the compound exhibits blue photo­luminescence and represents a promising candidate for a thermally stable and solvent-resistant blue fluorescent material.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617000213/eg3213sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617000213/eg3213Isup2.hkl
Contains datablock I

CCDC reference: 1525738

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2015) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Poly[(µ5-1,1'-biphenyl-2,2',4,4'-tetracarboxylato)bis[µ2-1,4-bis(1H-imidazol-1-yl)benzene]dizinc(II)] top
Crystal data top
[Zn2(C16H6O8)(C12H10N4)]F(000) = 1344
Mr = 667.18Dx = 1.767 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 9.4371 (11) ÅCell parameters from 3692 reflections
b = 18.909 (2) Åθ = 2.5–25.5°
c = 14.4981 (15) ŵ = 1.98 mm1
β = 104.162 (2)°T = 296 K
V = 2508.5 (5) Å3Block, colourless
Z = 40.28 × 0.26 × 0.20 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1877 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.033
φ and ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1111
Tmin = 0.608, Tmax = 0.693k = 2222
7259 measured reflectionsl = 1715
2345 independent reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0468P)2 + 4.1623P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2345 reflectionsΔρmax = 0.38 e Å3
191 parametersΔρmin = 0.64 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn11.00000.95384 (3)0.75000.03573 (18)
Zn20.50000.99870 (3)0.75000.03422 (18)
N10.4976 (3)0.93735 (17)0.8612 (2)0.0429 (7)
N20.4196 (3)0.85803 (16)0.9481 (2)0.0406 (7)
O10.8157 (3)1.01066 (13)0.72820 (19)0.0453 (6)
O20.6601 (2)1.06660 (14)0.79288 (18)0.0456 (6)
O30.9643 (3)1.08620 (15)1.12784 (18)0.0502 (7)
O41.1585 (3)1.15690 (17)1.16171 (18)0.0613 (8)
C11.0050 (3)1.14035 (17)0.8022 (2)0.0325 (7)
C20.9060 (3)1.10220 (17)0.8403 (2)0.0299 (7)
C30.9213 (3)1.09980 (18)0.9383 (2)0.0338 (7)
H30.85511.07390.96280.041*
C41.0341 (4)1.13561 (18)0.9995 (2)0.0338 (8)
C51.1272 (4)1.1762 (2)0.9614 (2)0.0443 (9)
H51.20131.20181.00170.053*
C61.1124 (4)1.1795 (2)0.8642 (2)0.0432 (9)
H61.17481.20820.84000.052*
C70.7862 (3)1.05702 (18)0.7819 (2)0.0331 (7)
C81.0574 (4)1.1277 (2)1.1056 (2)0.0404 (8)
C90.5868 (5)0.9380 (3)0.9515 (3)0.0652 (13)
H90.66750.96720.97250.078*
C100.5395 (5)0.8898 (3)1.0048 (3)0.0677 (13)
H100.58070.87991.06860.081*
C110.3987 (4)0.88905 (19)0.8622 (3)0.0441 (9)
H110.32320.87750.80990.053*
C120.3326 (4)0.80272 (18)0.9739 (3)0.0390 (8)
C130.3485 (4)0.7870 (2)1.0691 (3)0.0465 (9)
H130.41520.81201.11550.056*
C140.2345 (4)0.7658 (2)0.9049 (3)0.0449 (9)
H140.22430.77640.84090.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0346 (3)0.0404 (3)0.0334 (3)0.0000.0106 (2)0.000
Zn20.0251 (3)0.0410 (3)0.0355 (3)0.0000.0052 (2)0.000
N10.0380 (17)0.0485 (18)0.0402 (18)0.0035 (14)0.0058 (14)0.0074 (15)
N20.0423 (17)0.0428 (17)0.0362 (16)0.0099 (14)0.0085 (13)0.0069 (14)
O10.0322 (14)0.0498 (16)0.0526 (16)0.0010 (11)0.0079 (12)0.0197 (13)
O20.0278 (13)0.0556 (16)0.0552 (16)0.0063 (11)0.0135 (11)0.0196 (13)
O30.0540 (16)0.0601 (17)0.0368 (14)0.0092 (14)0.0120 (12)0.0075 (13)
O40.0644 (19)0.085 (2)0.0287 (14)0.0238 (17)0.0002 (13)0.0009 (14)
C10.0315 (18)0.0344 (17)0.0318 (18)0.0036 (14)0.0083 (14)0.0018 (14)
C20.0279 (17)0.0309 (17)0.0302 (17)0.0022 (14)0.0060 (13)0.0024 (14)
C30.0311 (17)0.0364 (18)0.0361 (19)0.0026 (15)0.0124 (14)0.0005 (15)
C40.0355 (19)0.0366 (18)0.0293 (17)0.0029 (15)0.0077 (14)0.0009 (14)
C50.048 (2)0.048 (2)0.034 (2)0.0193 (18)0.0045 (16)0.0034 (17)
C60.048 (2)0.048 (2)0.035 (2)0.0157 (18)0.0123 (17)0.0023 (17)
C70.0281 (17)0.0371 (18)0.0332 (18)0.0009 (14)0.0058 (14)0.0011 (15)
C80.042 (2)0.047 (2)0.0315 (19)0.0037 (18)0.0084 (16)0.0046 (17)
C90.050 (3)0.087 (3)0.050 (3)0.017 (2)0.003 (2)0.013 (2)
C100.060 (3)0.091 (4)0.042 (2)0.013 (3)0.007 (2)0.018 (2)
C110.046 (2)0.043 (2)0.038 (2)0.0059 (18)0.0007 (17)0.0069 (17)
C120.044 (2)0.0346 (18)0.040 (2)0.0151 (16)0.0139 (17)0.0076 (17)
C130.057 (2)0.043 (2)0.037 (2)0.0067 (18)0.0076 (18)0.0013 (17)
C140.058 (2)0.047 (2)0.0308 (19)0.0077 (19)0.0117 (17)0.0047 (17)
Geometric parameters (Å, º) top
Zn1—O3i1.879 (2)C1—C1iii1.493 (6)
Zn1—O3ii1.879 (2)C2—C31.394 (4)
Zn1—O12.002 (2)C2—C71.502 (4)
Zn1—O1iii2.002 (3)C3—C41.385 (5)
Zn2—O2iv1.964 (2)C3—H30.9300
Zn2—O21.964 (2)C4—C51.381 (5)
Zn2—N11.990 (3)C4—C81.506 (5)
Zn2—N1iv1.990 (3)C5—C61.383 (5)
N1—C111.308 (5)C5—H50.9300
N1—C91.374 (5)C6—H60.9300
N2—C111.347 (4)C9—C101.339 (6)
N2—C101.365 (5)C9—H90.9300
N2—C121.435 (5)C10—H100.9300
O1—C71.248 (4)C11—H110.9300
O2—C71.252 (4)C12—C141.377 (5)
O3—C81.277 (4)C12—C131.383 (5)
O3—Zn1ii1.879 (2)C13—C14v1.376 (5)
O4—C81.223 (4)C13—H130.9300
C1—C61.392 (5)C14—C13v1.376 (5)
C1—C21.397 (4)C14—H140.9300
O3i—Zn1—O3ii132.49 (17)C3—C4—C8120.2 (3)
O3i—Zn1—O196.84 (11)C4—C5—C6121.2 (3)
O3ii—Zn1—O1108.26 (12)C4—C5—H5119.4
O3i—Zn1—O1iii108.26 (12)C6—C5—H5119.4
O3ii—Zn1—O1iii96.84 (11)C5—C6—C1120.7 (3)
O1—Zn1—O1iii115.10 (15)C5—C6—H6119.7
O2iv—Zn2—O298.36 (16)C1—C6—H6119.7
O2iv—Zn2—N1118.49 (11)O1—C7—O2123.0 (3)
O2—Zn2—N1106.56 (12)O1—C7—C2119.9 (3)
O2iv—Zn2—N1iv106.56 (12)O2—C7—C2117.0 (3)
O2—Zn2—N1iv118.49 (11)O4—C8—O3125.6 (3)
N1—Zn2—N1iv108.69 (19)O4—C8—C4122.0 (3)
C11—N1—C9105.5 (3)O3—C8—C4112.4 (3)
C11—N1—Zn2124.4 (3)C10—C9—N1109.4 (4)
C9—N1—Zn2129.9 (3)C10—C9—H9125.3
C11—N2—C10106.1 (3)N1—C9—H9125.3
C11—N2—C12126.5 (3)C9—C10—N2107.2 (4)
C10—N2—C12127.4 (3)C9—C10—H10126.4
C7—O1—Zn1126.6 (2)N2—C10—H10126.4
C7—O2—Zn2123.1 (2)N1—C11—N2111.8 (3)
C8—O3—Zn1ii120.7 (2)N1—C11—H11124.1
C6—C1—C2118.1 (3)N2—C11—H11124.1
C6—C1—C1iii120.7 (3)C14—C12—C13120.4 (4)
C2—C1—C1iii121.2 (3)C14—C12—N2120.4 (3)
C3—C2—C1120.5 (3)C13—C12—N2119.2 (4)
C3—C2—C7115.6 (3)C14v—C13—C12120.0 (4)
C1—C2—C7123.7 (3)C14v—C13—H13120.0
C4—C3—C2120.6 (3)C12—C13—H13120.0
C4—C3—H3119.7C13v—C14—C12119.7 (3)
C2—C3—H3119.7C13v—C14—H14120.2
C5—C4—C3118.7 (3)C12—C14—H14120.2
C5—C4—C8121.0 (3)
C6—C1—C2—C34.3 (5)Zn1ii—O3—C8—C4161.8 (2)
C1iii—C1—C2—C3176.7 (3)C5—C4—C8—O40.3 (6)
C6—C1—C2—C7179.1 (3)C3—C4—C8—O4177.8 (4)
C1iii—C1—C2—C71.9 (5)C5—C4—C8—O3177.5 (3)
C1—C2—C3—C40.5 (5)C3—C4—C8—O30.0 (5)
C7—C2—C3—C4175.7 (3)C11—N1—C9—C100.1 (5)
C2—C3—C4—C52.8 (5)Zn2—N1—C9—C10176.2 (3)
C2—C3—C4—C8174.8 (3)N1—C9—C10—N20.2 (6)
C3—C4—C5—C62.3 (6)C11—N2—C10—C90.5 (5)
C8—C4—C5—C6175.3 (4)C12—N2—C10—C9179.5 (4)
C4—C5—C6—C11.6 (6)C9—N1—C11—N20.4 (4)
C2—C1—C6—C54.9 (5)Zn2—N1—C11—N2176.8 (2)
C1iii—C1—C6—C5176.1 (3)C10—N2—C11—N10.5 (4)
Zn1—O1—C7—O2144.6 (3)C12—N2—C11—N1179.4 (3)
Zn1—O1—C7—C232.6 (4)C11—N2—C12—C1413.7 (5)
Zn2—O2—C7—O113.4 (5)C10—N2—C12—C14166.2 (4)
Zn2—O2—C7—C2163.8 (2)C11—N2—C12—C13166.3 (3)
C3—C2—C7—O1122.0 (4)C10—N2—C12—C1313.8 (6)
C1—C2—C7—O153.1 (5)C14—C12—C13—C14v0.2 (6)
C3—C2—C7—O255.4 (4)N2—C12—C13—C14v179.8 (3)
C1—C2—C7—O2129.6 (4)C13—C12—C14—C13v0.2 (6)
Zn1ii—O3—C8—O416.0 (5)N2—C12—C14—C13v179.8 (3)
Symmetry codes: (i) x, y+2, z1/2; (ii) x+2, y+2, z+2; (iii) x+2, y, z+3/2; (iv) x+1, y, z+3/2; (v) x+1/2, y+3/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O4vi0.932.413.335 (5)171
Symmetry code: (vi) x1, y+2, z1/2.
 

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